


My Youth Is Yours

by Queenxo



Category: Teen Wolf (TV)
Genre: Alpha Derek Hale, Bottom Stiles Stilinski, Crossdressing, Emissary Stiles Stilinski, First Kiss, First Time, First Time Blow Jobs, Fluff, Idiots in Love, Loss of Virginity, M/M, Rimming, Smut, Stiles Stilinski in Panties, Top Derek Hale, Top Derek Hale/Bottom Stiles Stilinski, Virgin Stiles Stilinski
Language: English
Status: Completed
Published: 2020-09-28
Updated: 2020-09-28
Packaged: 2021-03-07 20:35:33
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,763
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26703805
Author URL: https://archiveofourown.org/users/Queenxo/pseuds/Queenxo
Summary: Derek climbs through Stiles window for advice and finds the teen in a dress.
Relationships: Derek Hale/Stiles Stilinski
Comments: 2
Kudos: 253





	My Youth Is Yours

**Author's Note:**

> hope everyone enjoys, comment and let me know what you think!

Stiles sits hunched over at his computer desk hands raking messily through his overgrown strands of sandy brown hair. The last couple of weeks had been a nightmare to put it nicely. Their ragtag pack of misfits were crippled under the unceasing cascade of the evil they were dealing with. It had all started with Gerard's defeat; they thought they could relax, almost everyone leaving for college. Stiles, however, stayed to help, unlike Scott, who had still left claiming he needed to get away from the darkness that was Beacon Hills. After the Nogitsune Stiles had wanted nothing more than to run as far and as fast as possible, he remained. Stiles stood steadfast at Derek's side as his Emissary in the face of all the evil the Nemeton could throw their way. The last year Stiles had been working vigorously to hone his spark, he had a chasm of untouched magical potential simmering beneath his skin, begging to be uncovered. 

Tonight was one of the countless nights where, regardless of how hard he tried, his magic refused to heed his call. The creek of the aged rusted hinges of his window pulling him from his self flagellating reverie.

Derek climbs through the window with well-practised ease, ease that comes from years of breaking into the teen's room via his never locked window. Derek huffs in annoyance, he had told the idiot to lock his window on numerous occasions, yet Stiles blatantly ignored the Alpha. 

"I know what you're going to say sour wolf, don't bother." Stiles throws over his shoulder, unphased by the Alphas imposing presence. Derek grunts watching as Stiles turns his chair in frustration levelling the Alpha with a tired glare. "Use your words big guy" Stiles states his tone betrays how frustrated the boy truly is, however, Derek doubts the frustration is aimed at him. 

"Dress" Derek grunts out, mouth dry. His eyes finally raking over the teen's body, Stile who would usually be found in a bad pun t-shirt, jeans and a plaid shirt was sat before him in a tight fitted dress. Finding Stiles attractive was not a new sensation for the older man, although the sight before him was. Stiles sat long legs sprawling from his desk chair, pink material clinging to his upper thigh, the legs themselves hairless. Derek wanted to caress the exposed skin with his large calloused palms. 

Stiles paled, his cheeks flaming as he stood up hurrying to find something appropriate to cover himself with. " Shit, shit, shit" Stiles mused as he flung himself around his room desperately. Fighting with the material of his dress as he attempted to cover more of the milky expanse of his bare thighs. 

"Stiles" Derek grumbled out, grabbing the boy by his shoulders and pulling him non too gently to stand before him. "Stop" the Alpha comanded, holding Stiles steady until he regained his balance. Stiles stood before him twitching nervously, his long dainty fingertips wrapped around the hem of his dress, futily adjusting it. 

"Just let me change Derek, I'm sorry." Stiles whispers, his voice wobbling with every word that passes his plush lips, his brown doe-like eyes welling with unshed tears as he stands fidgeting before the older man. 

"Stay" Derek growls out, eyes raking greedily over the expanse of Stiles body, Derek squeezes Stiles shoulders firmly in warning to stay still. His grip firm but not bruisingly so. Derek steps back a couple inches allowing himself an unobscured view of the younger man. 

Clinging tightly to Stiles body was a dusky pink, cold shoulder, long sleeve bodycon mini dress. Once over his initial shock of seeing the teen in a dress, he began to focus on the details. The dress hugged Stiles body sinfully, his pale mole speckled neck, shoulders and collarbone exposed to the Alpha. Derek wanted nothing more than to bury his fangs in the boy's sensitive skin. The Alpha craved to claim him. Seeing Stiles presented in such a way frayed his substantial self-control. Derek found himself growling low in his throat as he circled the boy hungrily drinking in every minute detail of his Emissary. 

"Der... Please" Stiles whimpered, his embarrassment evident. He felt the long line of warm heat as Derek nestled his body behind Stiles' his muscular torso pressed firmly to Stiles back. 

"What do you want, Stiles?" Derek growls into the boy's ear, his warm breath caressing the shell of Stiles' ear. Stiles shudders beneath him a whine fighting to break from his throat. Stiles bites back the pathetic need to beg for the Alpha to take him. 

"Let me change" Stiles whispers, mortified of being caught dressed this way by the man he had been in love with for years. Derek was the definition of a straight Alpha male and yet here Stiles was 18, gangly limbs wearing a pink dress in front of the man. Stiles had given up on the fantasy of having Derek long ago, knowing the Alpha would never settle for someone like him. Derek, with his rock hard abs and chiselled features, could have anyone he wanted why settle for a sarcastic teen with too many moles and a love for girls clothing. 

"What if I don't want you to?" Derek ask carefully, turning Stiles to face him, "What if I like it?" Derek's kaleidoscope eyes lock with Stiles' their warm breaths mingling in the sparse space between their lips. Derek brings a hand up to gently caress the side of Stiles' face his other possessively wrapping around Stiles' feminine waist, coming to rest above the round swell of the boy's ass. 

"Der..." Stiles starts cautiously realising he had no response. he was speechless in the Alphas secure hold. His breath coming in uncontrolled pants as he takes in the heavy presence of Derek's strong hands. "Why?" Stiles gasps out his eyes, swimming with confusion. 

Derek delights in the feel of the tight material beneath his palm, only wishing to replace it with Stiles pliant flesh. "Because I want you Stiles" Derek states as if it were a fact not realising the turmoil he was creating in Stiles' mind.

Stiles observes as Derek leans in their lips brushing before he presses one of his small dainty hands firmly against Derek's chest unspokenly asking the man to halt his actions. "Der we cant do this... I can't do this" Stiles states stepping away to create distance between their bodies. Stiles gulps deep lung fulls of the charged air of the room, closing his eyes and falling to slump on his bed. 

"I'm sorry Stiles" Derek apologises moving to sit next to the boy ensuring he leaves an appropriate amount of space to separate their bodies. He places a heavy hand on Stiles' shoulder comfortingly " Maybe we should discuss what I originally came here for?" Derek asks cautiously. 

"Yes, neutral ground, good I can do that!" Stiles exclaims twisting where is perched on the mattress to face the older man. "Lay it on me big guy" Stiles smiles up at Derek dopily the tension between the men dissipating."Oh wait, let me change first" Stiles states sheepishly mentally berating himself for becoming comfortable in his current attire while still in the Alphas presence. 

Derek's hand shoots out to grip the boy's wrist as he moves to stand. "Stiles" Derek whispers non verbally urging the younger man not to change. Stiles tugs his pink bottom lip between his teeth nipping at it as he mentally wrestles with himself over what to do. "Don't" Derek orders the rough pad of his thumb pulling the boy's lip from where its grasped between his teeth, Stiles gasps in surprise as Derek's thumb caresses across the red saliva slicked flesh of his bottom lip. 

Stiles' whisky brown eyes peer up at Derek through his long dark eyelashes. The calm air between them becoming charged in an instant as their eyes lock. "You're beautiful Stiles."

Stiles' lips part in shock hearing those words from Derek Hale as his thumb gently strokes back and forth against the corner of his mouth, the tip of Stiles' tongue grazing across the appendage as he wet his dry lips. he savours the taste of salt sitting heavily on the tip of his tongue. "Stiles" Derek growls warningly his already tumultuous control close to snapping.

Stiles blushes Derek growling his name sending a shiver through him, his cock twitching where it's confined within a pair of pink lace panties. "Yes, Alpha?" Stiles asks teasingly, eyelashes fluttering as he looks up at Derek coyly. 

Derek's firm hands grip Stiles by his curvy thighs, picking him up and tossing him to the head of the bed, the boys head bouncing against the cloud like the texture of his pillows. "Fuck Der..." Stiles whispers quiet enough that if it weren't for Derek's enhanced hearing, he would've missed it entirely. Derek slowly crawls up the length of Stiles body, savouring the way the boy whines prettily beneath him. 

"Are you sure, Stiles?" Derek asks his lips separated from Stiles by scant inches, his face hovering above the younger mans. Derek's rough palms glide up the length of Stiles' torso, the younger mans dress rucking up with the movement. Derek watches transfixed with every pale mole dotted inch of Stiles' thighs are exposed. 

"Please Der..." Stiles whines desperately, Derek presses his body firmly into Stiles' as he captures the boy's lips in a hungry kiss. Stiles moans into the older man's mouth, causing a responding growl to be ripped from the Alphas lips. Derek kisses down to the younger man's neck, sucking deep bruises into the sensitive flesh there. Delighting in the breathy moans extracted from the younger man. 

"What do you want?" Derek asked between sucking gentle bruises into the boy's defined collar bones. Derek licked and sucked at the skin greedily, savouring the taste of Stiles in his mouth. 

"I want you, Derek, all of you" Stiles moans eyes growing wide as one of his dexterous hands cups the Alphas hard length through the confines of his jeans. The man's hard cock sitting heavily in the boy's palm. "Can I taste you, Der?" Stiles asks eyes nervously flicking up to meet his, Stiles' pupil expanding till only a thin ring of his whisky brown iris' are visible. 

Derek grunts his affirmation flipping their bodies effortlessly until stiles' lithe body sits atop his lap. He grinds his substantial bulge against Stiles, watching as the boy's thighs spread, forcing his dress to bunch around his lean waist. Derek licks his lips hungrily as he watches the boys cock strain prettily against a pair of pretty pink lace panties. "Beautiful" Derek murmurs one of his sizeable fingertips teasingly trailing along the prominent bulge in the boy's panties. 

Stiles whimpers brokenly, moving down until his face hovers over Derek's crotch Stiles unzips the mans fly, shaky hands struggling to unclasp the button on the older man's jeans. One of Derek's warm hands encases Stiles' own, halting his movements. "Stiles we don't have to do this Derek assures the younger man not wanting him to feel pressurised into doing something he's not comfortable with. 

"I want to, I do its just..." Stiles pauses meeting Derek's eyes before quickly looking away in embarrassment. "I'm a virgin Der, everyone knows that" Stiles states bitterly. 

Derek grips Stiles under his arms, pulling the boy up until his face hovers above Dereks, Derek kisses him tenderly " I didn't" the man whispers into the kiss his voice filled with awe. "Why me?" 

Stiles buries his head in the warm heat of Derek's neck nuzzling against the Alpha. "It's stupid" Stiles whispers self depreciatingly against the Alphas skin. 

"Nothing about this is stupid Stiles, and you are the smartest person I know" Derek scratches at the boy's skull as he continues to nuzzle against his throat. 

Stiles pulls himself up onto straining arms, Dereks head resting bracketed between the younger man's hands as his eyes meet Stiles' nervous ones. Derek reaches up delicately caressing Stiles' cheek, his eyes brimming with an unusual fondness the boy was unaccustomed to. "I love you, Der, have for a while now." Stiles pauses drawing in a deep breath to maintain his quickly dissipating courage. " I want you to be the one to take my virginity, Alpha." 

Derek growls, pulling Stiles down until their lips meet, Stiles calling him Alpha, causing his eyes to flicker red, his blood felt like fire in his veins. Unrestrained desire coursing through him like wildfire. Derek licked and nipped at stiles' bottom lip pulling sweet moans from the boy. 

Confidence surging through him Stiles pops the button on Derek's jeans, lowering himself to nuzzle at the older man's constrained cock. Stiles mouths messily at the mans clothed erection before pulling down his boxers. Derek's erect length lays proudly against his belly, his tip flushed purple with need, his swollen balls nestled within dark coarse pubic hair. 

Stiles sucks timidly on the tip, lapping at the pool of precome collected there. Stiles moans taking the Alpha further into his mouth greedily lapping at the man's substantial length. Stiles moans around the man's cock, hastily swallowing the man deeper, tears springing in his eyes as he gags. Derek releases a guttural moan from the older man, his thick fingers entangling in the youngers hair, helping to guide him. 

Stiles pulls off, his lips disconnecting with an obscene pop. "Fuck me, Alpha?" Derek moans tugging Stiles until his body is nestled beneath his larger frame. Derek grinds his free erection against Stiles clothed one, pulling a broken moan from him. 

Derek divests the boy of his panties, pulling his dress over his head before slowly kissing his way down the younger mans soft, well-defined torso. Dereks neatly trimmed stubble, leaving red skin in its wake. "Turn over for me" Derek orders grinning, pleased as Stiles quickly complies with his order. 

Derek peppers the boys back with gentle kisses, trailing his way to the boys round ass. Derek slaps the inside of Stiles' thigh in silent instruction to spread his legs. Derek leans in lapping wetly at the boy tightly puckered hole. Derek growls relishing the taste of the boy's hole on his tongue. Derek pushes one of his digits between Stiles' lips, the boy greedily lapping at them. Once he deems them sufficiently wet, Derek pulls them from the boy's mouth. He circles the boy's hole with one of his sizeable wet fingers before pushing past the tight ring of muscle. "Fuck" Stiles groans out forehead pressed to the pillow. 

"Just tell me to stop if its too much" Derek instructs before adding a second finger beginning to scissor the boy, he slides his tongue in alongside the digits. 

"Please fuck me Der" Stiles moans "Please Alpha need you." Stiles pleads thrusting himself back onto Derek's fingers. A low growl rumbles in Derek's chest as he pulls his fingers from the boy's hole. Derek grips Stiles' hips in a bruising hold pulling them up until his entrance is flush with the aching head of his cock. 

Derek pushes in to the hilt, Stiles screams out his eyes screwed shut as stray tears escape, the boy falls limp in the Alphas hands whimpering brokenly. Derek begins to slowly thrust into the boy, broken whimpers turning to pleasured moans. 

"Fuck Der, more... Need more" Stiles whines his back arching beautifully as he fucks himself desperately on Derek's length. Derek reaches for the boy's throat pulling him up until his back is flush with Derek's torso. Sweat beads at Stiles brow as Derek thrusts punishingly into Stiles' heat. 

Stiles screams out heat curling in his gut as the tip of Derek's cock thrusts harshly against his prostate. "Mmmm close Der... Fuck" stiles groans out, Derek begins snapping his hips vigorously against the younger man's. 

Stiles spills over his stomach, hole clenching tightly around Derek, drawing his orgasm from him. Dereks come spilling warmth into Stiles' hole. Derek drapes himself over the boys back his breathing heavy as he comes down from his orgasm.

Stiles groans urging Derek to roll onto his back as he does he wraps a corded forearm around Stiles' dainty frame pulling the boy to lay against his chest, head tucked beneath Derek's chin. "I love you Stiles" Derek mutters sleepily as he protectively curls his body around Stiles', encasing the smaller man's body with his own. 

" I love you too Sourwolf" Stiles murmur pressing a sweet kiss to the man's sweat glistening chest, smiling dopily as he falls into a peaceful slumber wrapped safely in Derek Hales arms.


End file.
